At a Christmas party this month for his All-In podcast, David Sacks took to the stage sporting a Russian-style fur hat and was ceremoniously gifted a Vladimir Putin calendar and a box of caviar.
The Silicon Valley investor was riffing on his appointment last week as Donald Trump’s artificial intelligence and crypto “tsar”, while poking fun at critics who say his foreign policy attitudes align with those of the Russian leader.
The performance was classic Sacks, according to a number of people who know him: controversial, theatrical — and offensive to those who take him literally but irreverent and witty to those who do not.
Born in South Africa in 1972, Sacks made his name as part of the “PayPal mafia”, the group of founders and early employees at the payments company that includes Elon Musk and investors Peter Thiel, Keith Rabois and Reid Hoffman.
He has since launched a number of companies, a venture capital firm, the All-In podcast — on which he and three co-hosts discuss tech and politics — and found time to produce the satirical film, Thank you for Smoking. He has made personal investments in Uber, Airbnb and his old colleagues’ companies including Palantir, founded by Thiel, and Musk’s SpaceX.
Thiel recruited Sacks to the start-up that became PayPal in 1999. A year later the company merged with Musk’s X.com. In 2002 eBay decided to buy it.
“PayPal and its product were quicker, nimbler and better for consumers” than eBay’s own money-transfer capabilities, said one early investor in the payments group. “That was thanks to David.”
With the two companies struggling to agree on a price, eBay had been planning to launch a rival product to wipe out its rival. Then Sacks stepped in with a piece of corporate theatre.
The night before the inaugural “eBay Live” user conference, “we threw a huge party . . . where we invited eBay’s top sellers and gave them PayPal T-shirts”, said Vince Sollitto, whom Sacks recruited at PayPal having worked with him in the office of Republican congressman Christopher Cox in California.
“A procession of people wearing PayPal T-shirts turned up,” added Sallitto, saying eBay realised “if they killed us they would be killing their best customers . . . We credit that stunt with forcing their hand. Ebay called David and said: ‘We should talk’.”
A deal was done at a $1.5bn price tag. Flush from the sale, Sacks in 2006 founded his first company, a genealogy start-up. While it failed to take off, an internal messaging tool he had developed for it was spun out in 2008 as Yammer, which was sold to Microsoft four years later for $1.2bn, making Sacks his fortune.
The same month he turned 40, celebrating with a Marie Antoinette-themed party for a few hundred guests at a Los Angeles mansion. “Charlie Sheen gave the ‘roast’ and Snoop Dogg performed. It was a really fun event,” according to Sollitto.
In 2017, Sacks launched his venture capital firm Craft Ventures. The group has invested in multiple Musk companies, including xAI and X, formerly Twitter. When Musk took Twitter private in 2022, he asked Sacks to come in and help with the transition.
The pair are now set to work together again, with Musk tasked by Trump with running the newly formed Department of Government Efficiency. Musk’s exact remit, like that of Sacks, is vague.
Sacks will work to provide a clearer legal framework for crypto and AI, both of which he has invested in, alongside launching his own AI-powered start-up, Glue, this year. He has expressed support for open-source AI projects, where underlying code is publicly available, railed against censorship by AI companies and argued that they and other high-tech start-ups should play a central role in boosting US competitiveness and national security.
It is not clear how much direct power Sacks will have over those concerns. His new position is “an advisory role . . . which does not require David to leave Craft”, according to the firm.
Sacks also has a close relationship with vice-president-elect JD Vance, according to people with knowledge of their relationship. They added that Vance, who worked for Thiel earlier in his career, helped forge the link between Sacks and Trump.
But Sacks has also repeatedly clashed with rivals online and even his co-hosts and self-styled “besties” on his podcast over some of his more contentious opinions.
He has also been involved in some online spats, including this year with Paul Graham, the high-profile founder of start-up incubator Y Combinator, who suggested in a since-deleted post during an exchange on X that Sacks may be “the most evil person in Silicon Valley”. According to Sacks, he and Graham have never met.
The feuds have made Sacks a bête noire for those who disagree with his politics and occasionally caustic style.
“He believes the Ukraine war was precipitated by the west. He’s dogmatic, sure of his opinions,” said one acquaintance who has soured on Sacks. “He is so arrogant . . . so lacking in empathy for others.”
Sriram Krishnan, a former partner at venture firm Andreessen Horowitz who worked with Sacks on the Twitter transition, is more sympathetic. “David forms views from first-principles logic,” he said. “He doesn’t care if that means he’s disagreeing with a tribe of people.”
In public, Sacks can be simultaneously considered and provocative. A few months after Russia’s full-blown invasion of Ukraine, he argued for a peaceful resolution even if that meant acquiescing to some of Putin’s demands, in a piece headlined: “Neocons and the Woke Left Are Joining Hands and Leading Us to Woke War III”.
Sacks’s reputation for belligerence was a concern for Joseph Nelson when he was considering who to take investment from for his computer vision start-up Roboflow, a choice he described as “a one-way door in a company’s history”. But after speaking to Sacks, he was won over.
“The person David is on the pod or on Twitter is quite different to the person he is in the boardroom . . . You would be surprised at how much he listens, how pragmatic he is,” Nelson said.
Sacks’s politics are often compared to those of Thiel, who has become an intellectual beacon for libertarian-leaning technology workers in the Valley and beyond.
The pair met at Stanford University in the 1990s, and Sacks joined the Stanford Review, a conservative paper Thiel had established. In 1995, they co-wrote “The Diversity Myth”, a critique of the university’s efforts to promote multiculturalism at the expense — as the authors saw it — of other priorities.
Sacks and Thiel “were intellectually very close”, said the early PayPal investor. “The libertarian philosophy they have espoused was born of that era.”
Thiel was one of the earliest and most prominent tech investors to come out in support of Trump in 2016. Sacks joined later but just as fulsomely, hosting a $300,000-a-head fundraiser for the president-elect in June this year. A month later he was invited to talk at the Republican National Convention.
Sollitto insists Sacks is his own man rather than a Thiel acolyte. “I think they’re colleagues and peers,” he said. “David doesn’t need a guiding light: he’s very bright, very prescient.”
One prominent Silicon Valley investor who has clashed with Sacks on politics nonetheless celebrated his elevation to the role of Trump’s tsar. “We’ve disagreed publicly but he is really smart and having really smart people in government is good,” they said.
The mistake made by critics was to focus on Sacks’ style, rather than his substance, the investor added. Instead they should take Sacks seriously but not literally, an approach Thiel suggested in 2016 that the media take with Trump.
“Insiders tend to believe you have to be serious to be taken seriously,” they said. “But you have to be good at storytelling, you have to have charisma. Its so easy for boring bureaucrats to criticise while creating nothing.”